Premium
Skeletal rearrangement of 3‐methoxy‐ N ‐chloromorphinan
Author(s) -
Mohacsi E.,
Hayes T.
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190437
Subject(s) - chemistry , derivative (finance) , aqueous solution , ether , medicinal chemistry , degradation (telecommunications) , sodium hypochlorite , alkyl , ion , organic chemistry , telecommunications , computer science , financial economics , economics
3‐Methoxymorphinan ( 1 ) was converted to the corresponding N ‐chloro derivative 2 by treatment with aqueous sodium hypochlorite. Upon exposure to methanolic silver nitrate, 2 was rearranged to the carbinolamine ether 3 . In addition, considerable amounts of the dechlorinated morphinan 1 were formed. The structure of 3 was secured by spectral analysis and its degradation to the hexahydroindoline derivative 4 . The observed skeletal rearrangement of 2 which requires the migration of an alkyl group is discussed in terms of a nitrenium ion.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom